Choline hydroxide
Choline hydroxide
Names
IUPAC name
Choline hydroxide
Systematic IUPAC name
2-Hydroxy-N,N,N-trimethylethanaminium hydroxide[1]
Other names
  • Choline base
  • Ethanaminium, 2-hydroxy-N,N,N-trimethyl-, hydroxide (1:1)[1]
  • Gossypine[1]
  • (2-Hydroxyethyl)trimethylammonium hydroxide[1]
  • 2-Hydroxyethyl(trimethyl)azanium hydroxide[1]
  • Sincaline[1]
Identifiers
3D model (JSmol)
Abbreviations ChOH[2]
ChEMBL
ChemSpider
ECHA InfoCard 100.004.206
EC Number
UNII
  • InChI=1S/C5H14NO.H2O/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H2/q+1;/p-1
    Key: KIZQNNOULOCVDM-UHFFFAOYSA-M
  • C[N+](C)(C)CCO.[OH-]
Properties
[(CH3)3NCH2CH2OH]+OH−
Molar mass 121.180 g·mol−1
Appearance Viscous colorless deliquescent liquid[1][3] or white granular powder[4]
Odor Unpleasant, like trimethylamine[3]
Density 1.073 g/cm3 at 25 °C (46% water solution by weight)[5]
Very soluble[3]
Solubility 48-50% solution of choline hydroxide in water (by weight) is insoluble in toluene.[6] Choline hydroxide

is soluble in ethanol,[3] insoluble in diethyl ether and chloroform.[7]

1.4304 (46% water solution by weight)[5]
Structure
Tetrahedral at the nitrogen atom
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H314, H335, H372
P260, P261, P264, P270, P271, P280, P301+P330+P331, P302, P304+P340, P305, P316, P317, P319, P321, P338, P361, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
3
0
0
Flash point 92 °F (33 °C)[4]
380 °C (716 °F)[6]
Lethal dose or concentration (LD, LC):
21.4 mg/kg (mouse, intravenous)[1]
Related compounds
Other anions
 Choline chloride
Other cations
 Tetraethylammonium hydroxide
Related compounds
 Choline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Choline hydroxide is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+OH−. It is also known as choline base. It is used as solutions in water or alcohols, which are colorless and very alkaline.

Properties

It is hygroscopic and thus often encountered as a colorless viscous hydrated syrup that smells of trimethylamine (TMA). Aqueous solutions of choline are stable, but the compound slowly breaks down to ethylene glycol, polyethylene glycols, and TMA.[3]

Chemistry

Choline hydroxide is a quaternary ammonium salt, consisting of choline cations ([(CH3)3NCH2CH2OH]+) and hydroxide anions (OH−). It is bifunctional compound, meaning, it contains both quaternary ammonium functional group and a hydroxyl functional group. Choline hydroxide forms an ionic liquid.

Occurrence

The cation of this salt, choline, occurs in nature in living beings.[8]

Uses

Choline hydroxide is used in industry as a pH regulating agent[1] and as an eco-friendly, biodegradable, recyclable and efficient catalyst with high yields for synthesis of certain organic compounds (2-amino-3-nitro-4H-chromene derivatives) in an aqueous solution at room temperatures.[2]

A chemical reaction of various salicylaldehydes (2-hydroxybenzaldehydes) with (E)-N-methyl-1-(methylthio)-2-nitroethenamine, in the presence of a basic ionic liquid catalyst such as choline hydroxide, at room temperature in an aqueous medium, produces 2-amino-3-nitro-4H-chromene derivatives (yields up to 83-96%).[2]

Safety

Choline hydroxide irritates skin, eyes and respiratory system. It can cause serious injuries to the eyes. Causes serious skin and eye burns. Inhalation of this chemical may cause dyspnea and corrosive injuries to upper respiratory system and lungs, which can lead to pneumonia.[1][6][5] May react violently with strong oxidizing agents.[4]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 "Choline hydroxide". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 3 Krishnammagari, Suresh Kumar; Lim, Kwon Taek; Cho, Byung Gwon; Tae Jeong, Yeon (January 1, 2018). "Choline hydroxide: An efficient and biodegradable catalyst for the synthesis of 2-amino-3-nitro-4H-chromene derivatives in an aqueous medium". Phosphorus, Sulfur, and Silicon and the Related Elements. 193 (9): 574–581. doi:10.1080/10426507.2018.1469489. S2CID 105825055 – via www.sciencedirect.com.
  3. 1 2 3 4 5 Kirk RE, et al. (2000). Kirk-Othmer encyclopedia of chemical technology. Vol. 6 (4th ed.). John Wiley & Sons. pp. 100–102. ISBN 9780471484943.
  4. 1 2 3 "Choline hydroxide | 123-41-1". ChemicalBook.
  5. 1 2 3 https://www.sigmaaldrich.com/GB/en/product/aldrich/292257
  6. 1 2 3 https://www.carlroth.com/medias/SDB-3406-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMTA3NDN8YXBwbGljYXRpb24vcGRmfHNlY3VyaXR5RGF0YXNoZWV0cy9oMjcvaGFmLzkwNjA5OTcxMzY0MTQucGRmfGVmOTEwZTlkM2E0YTVjN2U4NWI0YzUxZWExNjRkYzFlYmE2YzYzMzRmOTU1NTc4MDA1NTBkZDkxY2U4NDY3M2Y
  7. ↑ Rucker RB, Zempleni J, Suttie JW, McCormick DB (2007). Handbook of vitamins (4th ed.). Taylor & Francis. pp. 459–477. ISBN 9780849340222.
  8. ↑ "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. Retrieved 11 November 2019.
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